Cyclo-hexyl-ammonium nitrate.

In the title salt, C6H14N(+)·NO3 (-), the cyclo-hexyl ring adopts a chair conformation. The ammonium group occupies an equatorial position and the crystal struture is stabilized by inter-molecular N-H⋯O hydrogen-bonding inter-actions, resulting in a three-dimensional network.

Related literature

For the Brønsted–Lowry basicity behavior of cyclo­hexyl­amine, see: Solomons (1996 ▶). For the preparation of salts of anions and complex anions with cyclo­hexyl primary ammonium cations, see: Jones et al. (1998 ▶); Kolev et al. (2007 ▶); Lock et al. (1981 ▶); Muthamizhchelvan et al. (2005 ▶); Wang et al. (2005 ▶); Yun et al. (2004 ▶). For precautions relating to the reaction of cyclo­hexyl­amine with strong acids or oxidizing agents, see: Chang (2008 ▶); Patnaik (2007 ▶). For the structures of other cyclo­hexyle­ammonium salts, see: Shimada et al. (1955 ▶); Smith et al. (1994 ▶); Odendal et al. (2010 ▶). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H14N+·NO3 −

M = 162.19

Monoclinic,

a = 8.9322 (9) Å

b = 9.9010 (9) Å

c = 10.3951 (10) Å

β = 103.866 (2)°

V = 892.53 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 294 K

0.39 × 0.15 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.964, T max = 0.987

2214 measured reflections

2214 independent reflections

1750 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.121

S = 1.09

2214 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814002244/sj5386sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002244/sj5386Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002244/sj5386Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H14N+·NO3−	F(000) = 352
Mr = 162.19	Dx = 1.207 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11857 reflections
a = 8.9322 (9) Å	θ = 2.4–28.3°
b = 9.9010 (9) Å	µ = 0.10 mm−1
c = 10.3951 (10) Å	T = 294 K
β = 103.866 (2)°	Block, colorless
V = 892.53 (15) Å3	0.39 × 0.15 × 0.14 mm
Z = 4

Bruker APEXII CCD diffractometer	2214 independent reflections
Radiation source: fine-focus sealed tube	1750 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.964, Tmax = 0.987	k = 0→13
2214 measured reflections	l = 0→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.0786P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.005
2214 reflections	Δρmax = 0.15 e Å−3
101 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (6)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.94737 (12)	0.24027 (11)	0.84734 (10)	0.0591 (3)
H1	1.0040	0.2396	0.9397	0.071*
H2	0.9334	0.1504	0.8165	0.071*
H3	1.0001	0.2818	0.8017	0.071*
C1	0.79115 (13)	0.30167 (11)	0.83331 (11)	0.0504 (3)
H4	0.7312	0.2428	0.8779	0.060*
C2	0.80481 (15)	0.43882 (13)	0.89905 (13)	0.0619 (3)
H5	0.8701	0.4967	0.8605	0.074*
H6	0.8523	0.4293	0.9928	0.074*
C3	0.64691 (18)	0.50274 (15)	0.88097 (18)	0.0806 (4)
H7	0.6580	0.5927	0.9190	0.097*
H8	0.5855	0.4495	0.9276	0.097*
C4	0.56468 (19)	0.51139 (15)	0.7354 (2)	0.0887 (5)
H9	0.4622	0.5482	0.7270	0.106*
H10	0.6208	0.5721	0.6906	0.106*
C5	0.55222 (17)	0.37454 (16)	0.67001 (17)	0.0833 (5)
H11	0.5052	0.3842	0.5762	0.100*
H12	0.4864	0.3168	0.7081	0.100*
C6	0.70975 (16)	0.30923 (13)	0.68820 (12)	0.0638 (3)
H13	0.6979	0.2189	0.6509	0.077*
H14	0.7716	0.3614	0.6412	0.077*
O1	0.90382 (12)	0.78324 (9)	0.87802 (9)	0.0694 (3)
O2	0.82965 (10)	0.96820 (10)	0.95391 (9)	0.0681 (3)
O3	0.87733 (12)	0.96351 (10)	0.75996 (9)	0.0729 (3)
N2	0.86827 (10)	0.90604 (10)	0.86507 (9)	0.0529 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0641 (6)	0.0561 (5)	0.0586 (6)	0.0105 (4)	0.0177 (4)	0.0154 (4)
C1	0.0543 (6)	0.0449 (5)	0.0521 (6)	0.0010 (4)	0.0129 (5)	0.0065 (4)
C2	0.0651 (7)	0.0546 (7)	0.0635 (7)	−0.0030 (5)	0.0108 (6)	−0.0057 (5)
C3	0.0777 (9)	0.0615 (8)	0.1048 (12)	0.0089 (7)	0.0265 (9)	−0.0157 (8)
C4	0.0674 (8)	0.0606 (8)	0.1274 (15)	0.0139 (7)	0.0022 (9)	0.0051 (8)
C5	0.0720 (8)	0.0705 (9)	0.0906 (10)	0.0057 (7)	−0.0135 (7)	0.0017 (8)
C6	0.0754 (8)	0.0569 (7)	0.0535 (7)	0.0052 (6)	0.0041 (6)	0.0008 (5)
O1	0.0868 (6)	0.0492 (5)	0.0696 (6)	0.0075 (4)	0.0139 (5)	0.0001 (4)
O2	0.0688 (5)	0.0736 (6)	0.0650 (5)	0.0105 (4)	0.0221 (4)	−0.0094 (4)
O3	0.0975 (7)	0.0663 (6)	0.0549 (5)	0.0129 (5)	0.0181 (5)	0.0090 (4)
N2	0.0479 (5)	0.0538 (5)	0.0536 (5)	0.0040 (4)	0.0051 (4)	−0.0018 (4)

N1—C1	1.4968 (15)	C3—H8	0.9700
N1—H1	0.9724	C4—C5	1.508 (2)
N1—H2	0.9440	C4—H9	0.9700
N1—H3	0.8498	C4—H10	0.9700
C1—C6	1.5112 (16)	C5—C6	1.519 (2)
C1—C2	1.5119 (17)	C5—H11	0.9700
C1—H4	0.9800	C5—H12	0.9700
C2—C3	1.5159 (19)	C6—H13	0.9700
C2—H5	0.9700	C6—H14	0.9700
C2—H6	0.9700	O1—N2	1.2556 (13)
C3—C4	1.518 (3)	O2—N2	1.2261 (12)
C3—H7	0.9700	O3—N2	1.2516 (13)
C1—N1—H1	110.6	H7—C3—H8	108.0
C1—N1—H2	107.8	C5—C4—C3	111.37 (13)
H1—N1—H2	108.9	C5—C4—H9	109.4
C1—N1—H3	112.2	C3—C4—H9	109.4
H1—N1—H3	109.1	C5—C4—H10	109.4
H2—N1—H3	108.2	C3—C4—H10	109.4
N1—C1—C6	109.37 (10)	H9—C4—H10	108.0
N1—C1—C2	110.38 (10)	C4—C5—C6	111.12 (12)
C6—C1—C2	111.97 (10)	C4—C5—H11	109.4
N1—C1—H4	108.3	C6—C5—H11	109.4
C6—C1—H4	108.3	C4—C5—H12	109.4
C2—C1—H4	108.3	C6—C5—H12	109.4
C1—C2—C3	110.31 (11)	H11—C5—H12	108.0
C1—C2—H5	109.6	C1—C6—C5	110.81 (12)
C3—C2—H5	109.6	C1—C6—H13	109.5
C1—C2—H6	109.6	C5—C6—H13	109.5
C3—C2—H6	109.6	C1—C6—H14	109.5
H5—C2—H6	108.1	C5—C6—H14	109.5
C2—C3—C4	111.14 (13)	H13—C6—H14	108.1
C2—C3—H7	109.4	O2—N2—O3	121.20 (10)
C4—C3—H7	109.4	O2—N2—O1	120.99 (10)
C2—C3—H8	109.4	O3—N2—O1	117.79 (10)
C4—C3—H8	109.4
N1—C1—C2—C3	178.21 (11)	C3—C4—C5—C6	−55.5 (2)
C6—C1—C2—C3	56.11 (15)	N1—C1—C6—C5	−178.51 (11)
C1—C2—C3—C4	−55.73 (16)	C2—C1—C6—C5	−55.83 (15)
C2—C3—C4—C5	56.08 (19)	C4—C5—C6—C1	55.08 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.97	1.89	2.8553 (14)	172
N1—H2···O3ii	0.94	1.97	2.9074 (15)	172
N1—H3···O1iii	0.85	2.24	2.9880 (15)	148
N1—H3···O3iii	0.85	2.28	3.0689 (15)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.97	1.89	2.8553 (14)	172
N1—H2⋯O3ii	0.94	1.97	2.9074 (15)	172
N1—H3⋯O1iii	0.85	2.24	2.9880 (15)	148
N1—H3⋯O3iii	0.85	2.28	3.0689 (15)	155

Symmetry codes: (i) ; (ii) ; (iii) .